You don’t need a coaching credential to have a coaching conversation. If you’ve ever sat with someone who was stuck, worried, or second‑guessing themselves—and you tried to help them think clearly—you’ve already done it.
A colleague says, “I messed up. I’m not cut out for this.”
A friend says, “I know what I should do… but what if I regret it?”
A family member says, “I always make the wrong call.”
There are two natural responses most people will take.
The first is correction: “That’s not true, you’re great.” The second is a quick fix: “Just quit.” “Just choose the safe option.” “Stop thinking and do it.”
Both are well‑meant. Both can also miss the real issue: the person isn’t only struggling with the decision. They’re struggling with the story that forms right after the decision—the meaning they attach to it, and what that meaning implies about who they are.
Robert Frost captured the human experience of this in his poem The Road Not Taken: a traveller chooses without knowing what lies ahead. You don’t need the poem’s details to use its insight. The point is simple.
When the future is unclear, the mind tries to make a complete picture anyway—and that picture can either steady us or trap us.
If you want to help people in a way that actually holds up after the conversation ends, here are two practical shifts.
1) Keep “what happened” separate from “what it means”
In everyday talk, facts and conclusions often arrive fused together:
“My manager didn’t reply, so I’m not valued.”
“I didn’t get the role, so I’m behind.”
“I chose this path, so the other one must have been better.”
Instead of debating the conclusion, expand the mind to evoke greater clarity by separating the layers.
Try: “Let’s split this into two parts: what happened, and what you’re making it mean.”
Then write two short lists:
What happened (what you can point to)
What it seems to mean (the conclusion)
This does something important: it gives the person room to think without feeling attacked. You’re not saying, “You’re wrong.” You’re saying, “Let’s see the full picture.”
A quick tell: listen for words that sound final—always, never, everyone, no one, too late, this proves… When you hear them, try this provocative inquiry:
“What is the truth in what you are saying?”
This invitation allows people to examine their thoughts.
2) Don’t reward speed and risk into action.
After a choice—or after a setback—people often want certainty fast. Not because the answer is fully tested, but because certainty brings relief.
There’s nothing wrong with wanting relief. The question is whether relief is quietly being mistaken for truth.
A useful distinction is:
Clarity of mind: “What do you mean by this?”
Certainty: “What can you do about that?”
When you engage prematurely in designing action, you risk people giving a standard or right answer that lacks ownership.
This isn’t slow for the sake of being slow. It prevents a temporary emotional need from turning into a permanent life conclusion.
Pausefully invite people to consider what they meant when they express an intention, and you be surprised seeing them finding words to express themselves.
The stance underneath both shifts
Good coaching in everyday life isn’t about winning an argument or delivering perfect advice. It’s about helping someone hold their story lightly:
accurate enough to respect reality,
flexible enough to update,
steady enough to guide action.
That’s “agency” in plain terms: the sense that I can do something from here, and I can revise as I learn.
Two invitations
If you want the deeper, research‑informed reflection behind these ideas—how perspective can feel solid while still being shaped—read the full reflective article on our site.
If you want to practise these skills with a clear method, feedback, and a group to practise alongside, explore the Transformative Edge program and learn how to coach people to achieve sustained, meaningful results.
